Bioconversion of Iodoacetophenones by Marine Fungi

Rocha, Lenilson C.; Luiz, Rodrigo F.; Rosset, Isac G.; Raminelli, Cristiano; Seleghim, Mirna Helena Regali; Sette, Lara Durães; Porto, André L. M.

doi:10.1007/s10126-012-9463-2

Cited by 17 publications

(9 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…An orange-red crystalline solid was obtained in 78% yield. The product was identified by spectroscopic data ( 1 H NMR, 13 C NMR and GC-MS, see Supplementary Information). Scheme 1 shows a synthesis of isatin 1 from aniline (first and second steps).…”

Section: Synthesis Of Indoline-23-dione (1)mentioning

confidence: 99%

“…The compound did not require further purification. The product was identified by spectroscopic data ( 1 H NMR, 13 C NMR and GC-MS, see Supplementary Information).…”

Section: Synthesis Of Standard Racemic Alcoholmentioning

confidence: 99%

“…11 This enzymatic versatility is essential for the adaptation and robustness of their metabolism to extreme conditions observed in the ocean, such as low temperatures, extreme variation of pH conditions, high salt concentration, high pressure and changes in ocean currents. 12 In addition, several marinederived fungi have been applied in the bioreduction of iodoacetophenones 13 and azido-ketones, 14 biohydrogenation of chalcones 15,16 as well as α,β-and α,β,γ,δ-unsaturated ketones, 17 and ene-reduction of Knoevenagel compounds. 18 In this study, the bioreduction of isatin 1 by whole cells of marine-derived fungi was performed to produce enantioenriched 3-hydroxyindolin-2-one 2.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

First Asymmetric Reduction of Isatin by Marine-Derived Fungi

Birolli¹,

Ferrreira²,

Jimenez³

et al. 2016

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

In this study, whole cells of marine-derived fungi were used to reduce isatin (1H-indole-2,3-dione) to dioxindole (3-hydroxyindolin-2-one) for 7 days at 32 °C. The screening showed that several strains could reduce isatin and produce the enantioenriched dioxindole. The best conversions were obtained by Cladosporium sp. CBMAI 1237 and Westerdykella sp. CBMAI 1679, however, the best enantiomeric excess was obtained only by Aspergillus sydowii CBMAI 935 (66% ee). In conclusion, marine-derived fungi show potential for asymmetric and chemoselective reduction of isatin (1H-indole-2,3-dione).

show abstract

Section: Synthesis Of Indoline-23-dione (1)mentioning

confidence: 99%

“…The compound did not require further purification. The product was identified by spectroscopic data ( 1 H NMR, 13 C NMR and GC-MS, see Supplementary Information).…”

Section: Synthesis Of Standard Racemic Alcoholmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

First Asymmetric Reduction of Isatin by Marine-Derived Fungi

Birolli¹,

Ferrreira²,

Jimenez³

et al. 2016

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…14 Literature reports that marine-derived organisms are sources of diverse enzymes suitable for biotransformation or biocatalytic reactions of organic compounds. 15 In addition, several marine sponge-derived fungi have been applied in the bioreduction of iodoacetophenones, 16 azido-ketones 17 and isatin. 18 However, to date, there is no report about the use of marine sponge's tissue in biotransformation reactions.…”

Section: Introductionmentioning

confidence: 99%

Biotechnological Properties of Sponges from Northeast Brazil: Cliona varians as a Biocatalyst for Enantioselective Reduction of Carbonyl Compounds

Riatto¹,

Victor²,

Sousa³

et al. 2018

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

To research the potential ability of whole marine sponges to act as biocatalysts, this paper describes for the first time the employment of whole Cliona varians sponge in the stereoselective reduction of prochiral α-keto esters and isatin to the corresponding chiral alcohols. The addition of D-fructose, D-glucose or sucrose remarkably increased the conversion ratios and stereoselectivities by this marine sponge. Furthermore, in the presence of D-glucose and D-maltose, the reduction of isatin by C. varians afforded the corresponding 3-hydroxyindolin-2-one with high conversions (85-90%) and good enantioselectivities (60-74%). These results showed that the marine sponge presents great potential to be used as biocatalyst for stereoselective reduction of carbonyl compounds.

show abstract

“…Na literatura, dados de RMN de 1 H para o ácido 2-metilfenilacético 5a, e dados correspondentes aos pontos de fusão para os ácidos 5a-7a corroboram com os dados apresentados pelos compostos biotransformados pelo fungo A. sysowii CBMAI 934 (LI e ALPER, 1986;BAIOCHI e GIANNANGELI, 1979;VAN DER STELT, HARMS e NAUTA, 1961). Para os ácidos 5a, 6a e 7a, além de análises de IV, RMN de 1 H e de 13 C, também, foram realizados análises iodofeniletanol (c = 25%, 24h), meta-e para-iodofeniletanol (c = 50%, 2h) por lipase de Candida antarctica (ROCHA et al, 2012;.…”

Section: Meounclassified

Hidrólise enzimática de nitrilas pelo fungo de origem marinha Aspergillus sydowii CBMAI 934

Oliveira¹

View full text Add to dashboard Cite

Meu agradecimento incondicional a Deus, pelo dom da vida, por direcionar o caminho que nela devo percorrer e pelas imensas oportunidades surgidas na minha jornada. Agradeço a Deus pela força que recebi para não desistir nos momentos de dificuldades surgidas ao longo desta caminhada. Aos meus pais, pela educação que me deram e por estarem sempre comigo, apoiando-me e transmitindo muito amor. Ao meu irmão Luzardo, por sempre estar aconselhando-me, apoiando-me e transmitindo-me muita confiança. Ao meu orientador Prof. Dr. André Luiz Meleiro Porto, pela oportunidade de trabalho, confiança e orientação. Ao Prof. Dr. Roberto G. S. Berlinck (IQSC) por ter cedido os micro-organismos utilizados neste trabalho. A Profa. Dra. Mirna H. R. Seleghim da UFSCar por ceder o espaço de seu laboratório para realizar um treinamento com manuseio de micro-organismos e a técnica Darci C. D. Javarotti pela dedicação em ensinar-me as técnicas de como trabalhar com micro-organismos. A Profa. Dra. Fernanda Canduri (IQSC) e a Prof. Dra. Cíntia D. L. Milagre (IQ-UNESP) pelas contribuições e discussões no decorrer deste trabalho. Ao Prof. Dr. Emanuel Carrilho por ter cedido seu laboratório para eu realizar as análises de eletroforese capilar. Aos técnicos dos aparelhos de Infravermelho (André Luiz-IQSC), Ressonância Magnética Nuclear (Silvana-IQSC), como também a Luciana Vizotto do Laboratório de RMN (UFSCar) pela obtenção dos espectros. Em particular ao Prof. Dr. Antônio Gilberto Ferreira (Giba) pela oportunidade de obter os espectros de RMN.

show abstract

Bioconversion of Iodoacetophenones by Marine Fungi

Cited by 17 publications

References 15 publications

First Asymmetric Reduction of Isatin by Marine-Derived Fungi

First Asymmetric Reduction of Isatin by Marine-Derived Fungi

Biotechnological Properties of Sponges from Northeast Brazil: Cliona varians as a Biocatalyst for Enantioselective Reduction of Carbonyl Compounds

Hidrólise enzimática de nitrilas pelo fungo de origem marinha Aspergillus sydowii CBMAI 934

Contact Info

Product

Resources

About